Tandem imine formation <i>via</i> auto-hydrogen transfer from alcohols to nitro compounds catalyzed by a nanomagnetically recyclable copper catalyst under solvent-free conditions

Pd/Cu‐catalyzed cross‐coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40–45 °C) provides α‐aryl(hetaryl)aminoacetylenic ketones in a yield of up to 97%. The latter undergo cyclization to 1,2,5‐triaryl(hetaryl)‐1,2‐dihydro‐3H‐pyrrol‐3‐ones in up to 93% yield after the treatment with KOH or Et2NH (40–55 °C, aqueous ethanol). The one‐pot synthesis of the pyrrol‐3‐ones (in up to 62% yields) by consecutive treatment of the above propargylamines with acyl chlorides (PdCl2/CuI/Ph3P) and a base (KOH) in aqueous ethanol has been also developed.

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Pd/Cu‐Catalyzed Cross‐Coupling of Densely Substituted Propargylamines with Aromatic Acyl Chlorides Followed by the Treatment with a Base: Access to Dihydro‐3H‐Pyrrol‐3‐Ones

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Volkov

Khrapova

et al. 2022

Adv Synth Catal

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Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

2021

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Pd-N-heterocyclic carbene complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K 4 [Fe(CN) 6 ]•3H 2 O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst offers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, easy catalyst recovery and reuse by successive extraction and final magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles.

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Synergistic effect between Co single atoms and nanoparticles enables selective synthesis of bio-based benzimidazoles

Wang

Zhang

et al. 2023

Applied Catalysis B: Environmental

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Tandem imine formation via auto-hydrogen transfer from alcohols to nitro compounds catalyzed by a nanomagnetically recyclable copper catalyst under solvent-free conditions

Abstract: A direct imination reaction was developed by tandem reaction of alcohols and nitro compounds in the presence of Cu-isatin Schiff base-γ-Fe2O3 as a nanomagnetically recyclable catalyst.

Cited by 9 publications

References 36 publications

Pd/Cu‐Catalyzed Cross‐Coupling of Densely Substituted Propargylamines with Aromatic Acyl Chlorides Followed by the Treatment with a Base: Access to Dihydro‐3H‐Pyrrol‐3‐Ones

Pd/Cu‐Catalyzed Cross‐Coupling of Densely Substituted Propargylamines with Aromatic Acyl Chlorides Followed by the Treatment with a Base: Access to Dihydro‐3H‐Pyrrol‐3‐Ones

Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

Synergistic effect between Co single atoms and nanoparticles enables selective synthesis of bio-based benzimidazoles

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